US12486236B2ActiveUtilityPatentIndex 50
Electroluminescent device
Assignee: BEIJING SUMMER SPROUT TECH CO LTDPriority: Jun 5, 2020Filed: Jun 4, 2021Granted: Dec 2, 2025
Est. expiryJun 5, 2040(~13.9 yrs left)· nominal 20-yr term from priority
Inventors:WANG LEWANG QIANGWANG JUNFEIZHANG HANZHANG QIDAI ZHIHONGZHANG CUIFANGLU NANNANKWONG CHI YUEN RAYMONDXIA CHUANJUN
H10K 50/11H10K 85/6572H10K 85/654H10K 85/342C07F 15/0086H10K 50/12H10K 85/631H10K 85/615H10K 2101/10C07F 15/0033C07D 223/32
50
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0
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30
Claims
Abstract
Provided is an electroluminescent device. The electroluminescent device includes an anode, a cathode and an organic layer disposed between the anode and the cathode, where the organic layer includes at least a first compound having a structure of H-L-E and a second compound having a general formula of M(L a ) m (L b ) n (L c ) q . The novel material combination consisting of the first compound and the second compound can enable the electroluminescent device to obtain a lower voltage, higher efficiency and an ultra-long lifetime and can provide better device performance. Further provided are a display assembly and a compound combination.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1 . An electroluminescent device, comprising:
an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises at least a first compound and a second compound; the first compound has a structure of H-L-E; H has a structure represented by Formula 1-a:
in Formula 1-a, A 1 , A 2 and A 3 are, at each occurrence identically or differently, selected from CR, and F 1 to F 10 are, at each occurrence identically or differently, selected from CR f ; and
E has a structure represented by Formula 2-d:
in Formula 2-d, Z 2 and Z 4 are each independently selected from CR z ;
L is selected from substituted or unsubstituted arylene having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene having 3 to 30 carbon atoms or a combination thereof;
R, R f and R z are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, a cyano group, a hydroxyl group, a sulfanyl group, and combinations thereof; and
adjacent substituents R, R f can be optionally joined to form a ring;
the second compound is a metal complex having a general formula of Ir(L a ) 2 (L b );
wherein,
L a and L b are a first ligand and a second ligand coordinated to the Ir, respectively; L a and L b can be optionally joined to form a multidentate ligand;
the multiple L a may be the same or different;
the L a has a structure represented by Formula 3-1 or Formula 3-3:
wherein,
the ring E is selected from a benzene ring;
R e represents, at each occurrence identically or differently, mono-substitution, multiple substitutions or non-substitution;
X 11 to X 14 are, at each occurrence identically or differently, selected from CR x1 ; X 31 to X 34 are, at each occurrence identically or differently, selected from CR x3 ;
Y 3 and Y 4 are, at each occurrence identically or differently, selected from CR d ;
R x1 , R x3 , R d and R e are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, and combinations thereof;
adjacent substituents R x1 , R d and R e can be optionally joined to form a ring;
when R x3 is selected from substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, or substituted or unsubstituted amino having 0 to 20 carbon atoms, adjacent substituents R x3 can be optionally joined to form a ring;
L b is selected from the following structure:
R a , R b and R c represent, at each occurrence identically or differently, mono-substitution, multiple substitutions or non-substitution;
X c and X d are O;
R a , R b and R c , are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, a cyano group, and combinations thereof;
in structures of L b , adjacent substituents R a , R b , R c , can be optionally joined to form a ring; and, the following case is not comprised: the first compound is
while the second compound is
2 . The electroluminescent device of claim 1 , wherein the H has a structure represented by Formula 1-a:
wherein A 1 to A 3 are, at each occurrence identically or differently, selected from CR, and F 1 to F 10 are, at each occurrence identically or differently, selected from CR f ; wherein
R and R f are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, a cyano group, a hydroxyl group, a sulfanyl group, and combinations thereof;
adjacent substituents R, R f can be optionally joined to form a ring.
3 . The electroluminescent device of claim 1 , wherein the H is selected from the group consisting of the following structures:
wherein optionally, hydrogens in the above structures can be partially or fully substituted with deuterium.
4 . The electroluminescent device of claim 3 , wherein the E is selected from the group consisting of the following structures:
wherein in the above structures, represents the position where the structure is joined to the structure of L;
wherein optionally, hydrogens in the above structures can be partially or fully substituted with deuterium.
5 . The electroluminescent device of claim 4 , wherein the L is selected from the group consisting of the following structures:
wherein in the above structures, “*” represents the position where the structure is joined to the structure of H, and represents the position where the structure is joined to the structure of E;
wherein optionally, hydrogens in the above structures can be partially or fully substituted with deuterium.
6 . The electroluminescent device of claim 5 , wherein the first compound is selected from the group consisting of the following Compounds, wherein the Compounds have the structure of H-L-E, wherein H, L and E are respectively selected from structures in the following table:
Compound
No.
H
L
E
1-2
H-1
L-1
E-1
1-59
H-1
L-1
E-2
1-60
H-1
L-1
E-3
1-61
H-1
L-1
E-4
1-62
H-1
L-1
E-5
1-63
H-1
L-1
E-6
1-64
H-1
L-1
E-7
1-65
H-1
L-1
E-8
1-66
H-1
L-1
E-9
1-67
H-1
L-1
E-10
1-68
H-1
L-1
E-36
1-69
H-1
L-1
E-37
1-70
H-1
L-1
E-38
1-71
H-1
L-1
E-39
1-72
H-1
L-1
E-40
1-73
H-1
L-1
E-41
1-74
H-1
L-1
E-42
1-75
H-1
L-1
E-43
1-76
H-1
L-1
E-44
1-77
H-1
L-2
E-15
1-78
H-1
L-2
E-2
1-79
H-1
L-2
E-3
1-80
H-1
L-2
E-4
1-81
H-1
L-2
E-5
1-82
H-1
L-2
E-6
1-83
H-1
L-2
E-7
1-84
H-1
L-2
E-8
1-85
H-1
L-2
E-9
1-86
H-1
L-2
E-10
1-87
H-1
L-2
E-45
1-88
H-1
L-2
E-46
1-89
H-1
L-2
E-47
1-90
H-1
L-2
E-48
1-91
H-1
L-3
E-49
1-92
H-1
L-3
E-50
1-93
H-1
L-3
E-51
1-94
H-1
L-3
E-52
1-95
H-1
L-3
E-53
1-96
H-1
L-3
E-54
1-97
H-1
L-3
E-55
1-98
H-1
L-3
E-56
1-99
H-1
L-3
E-57
1-100
H-1
L-3
E-58
1-101
H-1
L-3
E-1
1-102
H-1
L-3
E-2
1-103
H-1
L-4
E-3
1-104
H-1
L-4
E-4
1-105
H-1
L-4
E-5
1-106
H-1
L-4
E-6
1-107
H-1
L-4
E-7
1-108
H-1
L-4
E-8
1-109
H-1
L-4
E-9
1-110
H-1
L-4
E-10
1-111
H-1
L-4
E-40
1-112
H-1
L-4
E-41
1-113
H-1
L-4
E-42
1-114
H-1
L-4
E-43
1-115
H-1
L-4
E-44
1-116
H-1
L-4
E-45
1-117
H-1
L-5
E-46
1-118
H-1
L-5
E-47
1-119
H-1
L-5
E-48
1-120
H-1
L-5
E-49
1-121
H-1
L-5
E-50
1-122
H-1
L-5
E-51
1-123
H-1
L-5
E-52
1-124
H-1
L-5
E-53
1-125
H-1
L-5
E-54
1-126
H-1
L-5
E-55
1-127
H-1
L-5
E-56
1-128
H-1
L-5
E-57
1-129
H-1
L-5
E-58
1-130
H-1
L-5
E-1
1-131
H-1
L-5
E-2
1-132
H-1
L-5
E-3
1-133
H-1
L-6
E-4
1-134
H-1
L-6
E-5
1-135
H-1
L-6
E-6
1-136
H-1
L-6
E-7
1-137
H-1
L-6
E-8
1-138
H-1
L-6
E-9
1-139
H-1
L-6
E-10
1-140
H-1
L-6
E-36
1-141
H-1
L-6
E-37
1-142
H-1
L-6
E-38
1-143
H-1
L-6
E-39
1-144
H-1
L-6
E-40
1-145
H-1
L-7
E-41
1-146
H-1
L-7
E-42
1-147
H-1
L-7
E-43
1-148
H-1
L-7
E-44
1-149
H-1
L-7
E-45
1-150
H-1
L-7
E-46
1-151
H-1
L-7
E-47
1-152
H-1
L-8
E-1
1-153
H-1
L-8
E-2
1-154
H-1
L-8
E-3
1-155
H-1
L-8
E-4
1-156
H-1
L-8
E-5
1-157
H-1
L-8
E-6
1-158
H-1
L-8
E-7
1-159
H-1
L-8
E-8
1-160
H-1
L-8
E-9
1-161
H-1
L-8
E-10
1-162
H-1
L-8
E-11
1-164
H-1
L-8
E-13
1-166
H-1
L-9
E-15
1-167
H-1
L-9
E-16
1-187
H-1
L-11
E-36
1-188
H-1
L-11
E-37
1-189
H-1
L-11
E-38
1-190
H-1
L-11
E-39
1-191
H-1
L-12
E-1
1-192
H-1
L-12
E-2
1-193
H-1
L-12
E-3
1-194
H-1
L-12
E-4
1-195
H-1
L-12
E-5
1-196
H-1
L-12
E-6
1-197
H-1
L-12
E-7
1-198
H-1
L-12
E-8
1-199
H-1
L-12
E-9
1-200
H-1
L-12
E-10
1-201
H-1
L-12
E-36
1-202
H-1
L-12
E-37
1-203
H-1
L-12
E-38
1-204
H-1
L-12
E-39
1-205
H-1
L-12
E-40
1-206
H-1
L-12
E-41
1-207
H-1
L-13
E-1
1-208
H-1
L-13
E-2
1-209
H-1
L-13
E-3
1-210
H-1
L-13
E-4
1-211
H-1
L-13
E-5
1-212
H-1
L-13
E-6
1-213
H-1
L-13
E-7
1-214
H-1
L-13
E-8
1-215
H-1
L-13
E-9
1-216
H-1
L-13
E-10
1-217
H-1
L-13
E-50
1-218
H-1
L-13
E-51
1-219
H-1
L-13
E-52
1-220
H-1
L-13
E-53
1-221
H-1
L-13
E-54
1-222
H-1
L-14
E-1
1-223
H-1
L-14
E-2
1-224
H-1
L-14
E-3
1-225
H-1
L-14
E-4
1-226
H-1
L-14
E-5
1-227
H-1
L-14
E-6
1-228
H-1
L-14
E-7
1-229
H-1
L-14
E-8
1-230
H-1
L-14
E-9
1-231
H-1
L-14
E-10
1-232
H-1
L-14
E-38
1-233
H-1
L-14
E-39
1-234
H-1
L-14
E-40
1-235
H-1
L-14
E-41
1-236
H-1
L-14
E-42
1-237
H-1
L-14
E-43
1-238
H-1
L-14
E-44
1-239
H-1
L-14
E-45
1-240
H-1
L-14
E-46
1-241
H-1
L-14
E-47
1-242
H-1
L-15
E-1
1-243
H-1
L-15
E-2
1-244
H-1
L-15
E-3
1-245
H-1
L-15
E-4
1-246
H-1
L-15
E-5
1-247
H-1
L-15
E-6
1-248
H-1
L-15
E-7
1-249
H-1
L-15
E-8
1-250
H-1
L-15
E-9
1-251
H-1
L-15
E-10
1-252
H-1
L-15
E-44
1-253
H-1
L-15
E-45
1-254
H-1
L-15
E-46
1-255
H-1
L-15
E-47
1-256
H-1
L-15
E-48
1-257
H-1
L-15
E-49
1-258
H-1
L-16
E-1
1-259
H-1
L-16
E-2
1-260
H-1
L-16
E-3
1-261
H-1
L-16
E-4
1-262
H-1
L-16
E-5
1-263
H-1
L-16
E-6
1-264
H-1
L-16
E-7
1-265
H-1
L-16
E-8
1-266
H-1
L-16
E-9
1-267
H-1
L-16
E-10
1-268
H-1
L-16
E-45
1-269
H-1
L-16
E-46
1-270
H-1
L-16
E-47
1-271
H-1
L-16
E-48
1-272
H-1
L-16
E-49
1-273
H-1
L-16
E-50
1-274
H-1
L-16
E-51
1-275
H-1
L-17
E-1
1-276
H-1
L-17
E-2
1-277
H-1
L-17
E-3
1-278
H-1
L-17
E-4
1-279
H-1
L-17
E-5
1-280
H-1
L-17
E-6
1-281
H-1
L-17
E-7
1-282
H-1
L-17
E-8
1-283
H-1
L-17
E-9
1-284
H-1
L-17
E-10
1-285
H-1
L-17
E-36
1-286
H-1
L-17
E-37
1-287
H-1
L-17
E-38
1-288
H-1
L-17
E-39
1-289
H-1
L-17
E-40
1-290
H-1
L-17
E-41
1-291
H-1
L-17
E-42
1-292
H-1
L-17
E-43
1-293
H-1
L-17
E-44
1-294
H-1
L-17
E-45
1-295
H-1
L-17
E-46
1-296
H-1
L-17
E-47
1-297
H-1
L-17
E-48
1-298
H-1
L-17
E-49
1-299
H-1
L-17
E-50
1-300
H-1
L-17
E-51
1-357
H-1
L-18
E-1
1-358
H-1
L-18
E-2
1-359
H-1
L-18
E-3
1-360
H-1
L-18
E-4
1-361
H-1
L-18
E-5
1-362
H-1
L-18
E-6
1-363
H-1
L-18
E-7
1-364
H-1
L-18
E-8
1-365
H-1
L-18
E-9
1-366
H-1
L-18
E-10
1-367
H-1
L-18
E-11
1-369
H-1
L-18
E-13
1-371
H-1
L-18
E-15
1-372
H-1
L-18
E-16
1-379
H-1
L-19
E-1
1-380
H-1
L-19
E-2
1-381
H-1
L-19
E-3
1-382
H-1
L-19
E-4
1-383
H-1
L-19
E-5
1-384
H-1
L-19
E-6
1-385
H-1
L-19
E-7
1-386
H-1
L-19
E-8
1-387
H-1
L-19
E-9
1-388
H-1
L-19
E-10
1-389
H-1
L-19
E-11
1-391
H-1
L-19
E-13
1-393
H-1
L-19
E-15
1-394
H-1
L-19
E-16
1-401
H-1
L-20
E-10
1-402
H-1
L-20
E-11
1-403
H-1
L-20
E-12
1-404
H-1
L-20
E-13
1-406
H-1
L-20
E-15
1-407
H-1
L-20
E-16
1-423
H-49
L-1
E-11
1-425
H-49
L-3
E-13
1-427
H-49
L-5
E-15
1-428
H-49
L-6
E-16
1-436
H-49
L-14
E-1
1-437
H-49
L-15
E-1
1-438
H-49
L-16
E-1
1-439
H-49
L-17
E-1
1-440
H-49
L-18
E-1
1-441
H-49
L-19
E-1
1-442
H-49
L-20
E-1
1-511
H-1
L-21
E-1
1-512
H-1
L-22
E-1
1-513
H-1
L-23
E-1
1-514
H-1
L-24
E-1
1-515
H-1
L-25
E-1
1-516
H-1
L-26
E-1
1-517
H-1
L-27
E-1
1-518
H-1
L-28
E-1
1-519
H-1
L-1
E-69
1-520
H-1
L-12
E-69.
7 . The electroluminescent device of claim 1 , wherein the E has a structure represented by Formula 2-d:
wherein Z 2 and Z 4 are, at each occurrence identically or differently, selected from CR z ;
wherein R z is, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, a cyano group, and combinations thereof.
8 . The electroluminescent device of claim 7 , wherein R z is, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, phenyl, naphthyl, biphenyl, terphenyl, fluorenyl, dibenzofuranyl, dibenzothienyl, pyridyl and combinations thereof.
9 . The electroluminescent device of claim 1 , wherein in the first compound, the L is selected from substituted or unsubstituted arylene having 6 to 30 carbon atoms.
10 . The electroluminescent device of claim 9 , wherein the L is selected from the group consisting of: phenylene, naphthylene, biphenylene, terphenylene, triphenylenylene, phenanthrylene and fluorenylidene.
11 . The electroluminescent device of claim 1 , wherein in the second compound, the L a has a structure represented by Formula 3-1 or Formula 3-3:
wherein,
the ring E is selected from a benzene ring;
R e represents, at each occurrence identically or differently, mono-substitution, multiple substitutions or non-substitution;
X 11 to X 14 are, at each occurrence identically or differently, selected from CR x1 ; X 31 to X 34 are, at each occurrence identically or differently, selected from CR x3 ;
Y 3 and Y 4 are, at each occurrence identically or differently, selected from CR d ;
R x1 , R x3 , R d and R e are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, a cyano group, a hydroxyl group, a sulfanyl group, and combinations thereof;
adjacent substituents R x1 , R d and R e can be optionally joined to form a ring;
when R x3 is selected from substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms or substituted or unsubstituted amino having 0 to 20 carbon atoms, adjacent substituents R x3 can be optionally joined to form a ring.
12 . The electroluminescent device of claim 1 , wherein L a has a structure represented by Formula 3-6, Formula 3-8 or Formula 3-9:
wherein
X 11 to X 14 are, at each occurrence identically or differently, selected from CR x1 ; X 31 to X 34 are, at each occurrence identically or differently, selected from CR x3 ;
Y 3 and Y 4 are, at each occurrence identically or differently, selected from CR d ;
Y 5 , Y 6 , Y 7 and Y 8 are, at each occurrence identically or differently, selected from CR e ;
R x1 , R x3 , R d and R e are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, a cyano group, a hydroxyl group, a sulfanyl group, and combinations thereof;
adjacent substituents R x1 , R d and R e can be optionally joined to form a ring;
when R x3 is selected from substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms or substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, or substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, adjacent substituents R x3 can be optionally joined to form a ring.
13 . The electroluminescent device of claim 12 , wherein in Formula 3-6, Formula 3-8 or Formula 3-9, Y 3 and/or Y 4 are/is selected from CR d , and the R a is, at each occurrence identically or differently, selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, a cyano group, a hydroxyl group, a sulfanyl group, and combinations thereof.
14 . The electroluminescent device of claim 12 , wherein in Formula 3-6, Formula 3-8 or Formula 3-9, at least one or two of Y 5 to Y 8 are selected from CR e , and the R e is, at each occurrence identically or differently, selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, a cyano group, a hydroxyl group, a sulfanyl group, and combinations thereof.
15 . The electroluminescent device of claim 14 , wherein in Formula 3-6 and Formula 3-9, Y 6 is selected from CR e ; in Formula 3-8, Y 4 is selected from CR d and/or at least one of Y 6 to Y 8 is selected from CR e ;
and, the R d and R e are, at each occurrence identically or differently, selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, a cyano group, a hydroxyl group, a sulfanyl group, and combinations thereof.
16 . The electroluminescent device of claim 15 , wherein the R d and R e are, at each occurrence identically or differently, selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, and combinations thereof.
17 . The electroluminescent device of claim 12 , wherein in Formula 3-6, Formula 3-8 or Formula 3-9, at least one or two of X 11 to X 14 are selected from CR x1 , at least one or two of X 31 to X 34 are selected from CR x3 , and the R x1 and R x3 are, at each occurrence identically or differently, selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, a cyano group, a hydroxyl group, a sulfanyl group, and combinations thereof.
18 . The electroluminescent device of claim 17 , wherein in Formula 3-6, Formula 3-8 or Formula 3-9, X 12 and/or X 14 are/is selected from CR x1 , X 32 and/or X 34 are/is selected from CR x3 , and the R x1 and R x3 are, at each occurrence identically or differently, selected from the group consisting of: substituted or unsubstituted alkyl having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms and combinations thereof.
19 . The electroluminescent device of claim 18 , wherein in Formula 3-6, Formula 3-8 or Formula 3-9, X 12 and X 14 are each independently selected from CR x1 , X 32 and X 34 are each independently selected from CR x3 , and the R x1 and R x3 are, at each occurrence identically or differently, selected from the group consisting of: deuterium, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, cyclopentyl, cyclohexyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated t-butyl, deuterated cyclopentyl, deuterated cyclohexyl and combinations thereof.
20 . The electroluminescent device of claim 1 , wherein L a is, at each occurrence identically or differently, selected from the group consisting of the following structures:
L a-35
L a-36
L a-37
L a-38
L a-39
L a-40
L a-41
L a-42
L a-43
L a-44
L a-45
L a-46
L a-47
L a-48
L a-49
L a-50
L a-51
L a-52
L a-53
L a-54
L a-55
L a-56
L a-57
L a-58
L a-59
L a-60
L a-61
L a-62
L a-63
L a-64
L a-65
L a-66
L a-67
L a-68
L a-69
L a-70
L a-71
L a-72
L a-73
L a-74
L a-75
L a-76
L a-77
L a-78
L a-79
L a-80
L a-81
L a-82
L a-83
L a-84
L a-85
L a-86
L a-87
L a-88
L a-89
L a-90
L a-91
L a-92
L a-93
L a-94
L a-95
L a-96
L a-97
L a-98
L a-99
L a-100
L a-101
L a-102
L a-103
L a-104
L a-105
L a-106
L a-107
L a-108
L a-109
L a-110
L a-111
L a-112
L a-113
L a-114
L a-115
L a-116
L a-117
L a-118
L a-119
L a-120
L a-121
L a-122
L a-123
L a-124
L a-125
L a-126
L a-127
L a-128
L a-129
L a-130
L a-131
L a-132
L a-133
L a-134
L a-135
L a-136
L a-137
L a-138
L a-139
L a-140
L a-141
L a-142
L a-143
L a-144
L a-145
L a-146
L a-147
L a-148
L a-149
L a-150
L a-151
L a-152
L a-153
L a-154
L a-155
L a-156
L a-157
L a-158
L a-159
L a-160
L a-161
L a-162
L a-163
L a-164
L a-165
L a-166
L a-167
L a-168
L a-169
L a-170
L a-171
L a-172
L a-173
L a-174
L a-175
L a-176
L a-177
L a-178
L a-179
L a-180
L a-181
L a-182
L a-183
L a-184
L a-185
L a-186
L a-187
L a-188
L a-189
L a-190
L a-191
L a-192
L a-193
L a-194
L a-195
L a-196
L a-197
L a-198
L a-199
L a-200
L a-201
L a-202
L a-203
L a-204
L a-205
L a-206
L a-207
L a-208
L a-209
L a-210
L a-211
L a-212
L a-213
L a-214
L a-215
L a-216
L a-217
L a-218
L a-219
L a-220
L a-221
L a-222
L a-223
21 . The electroluminescent device of claim 20 , wherein the L b has a structure represented by Formula 4:
wherein R 1 to R 7 are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, a cyano group, and combinations thereof.
22 . The electroluminescent device of claim 21 , wherein at least two of R 1 to R 3 are, at each occurrence identically or differently, selected from substituted or unsubstituted alkyl having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms or a combination thereof; and/or at least two of R 4 to R 6 are, at each occurrence identically or differently, selected from substituted or unsubstituted alkyl having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms or a combination thereof.
23 . The electroluminescent device of claim 20 , wherein the L b is, at each occurrence identically or differently, selected from the group consisting of the following:
24 . The electroluminescent device of claim 23 ,
wherein the second compound is selected from the group consisting of Compound 2-1 to Compound 2-2, Compound 2-5 to Compound 2-26, Compound 2-41 to Compound 2-62, Compound 2-77 to Compound 2-98, Compound 2-113 to Compound 2-134, Compound 2-149 to Compound 2-170, Compound 2-185 to Compound 2-206, Compound 2-217 to Compound 2-223, Compound 2-229 to Compound 2-237, Compound 2-243 to Compound 2-251, Compound 2-257 to Compound 2-265, Compound 2-271 to Compound 2-279, Compound 2-285 to Compound 2-293 and Compound 2-299 to Compound 2-300; wherein, the Compound 2-1 to Compound 2-2, Compound 2-5 to Compound 2-26, Compound 2-41 to Compound 2-62, Compound 2-77 to Compound 2-98, Compound 2-113 to Compound 2-134, Compound 2-149 to Compound 2-170, Compound 2-185 to Compound 2-206 have the structure of Ir(L a ) 2 (L b ), wherein the two L a are the same, and the L a and L b are respectively selected from structures listed in the following table:
Compound
Compound
No.
L a
L b
No.
L a
L b
2-1
L a-36
L b1
2-2
L a-133
L b1
2-5
L a-36
L b31
2-6
L a-37
L b31
2-7
L a-41
L b31
2-8
L a-43
L b31
2-9
L a-45
L b31
2-10
L a-53
L b31
2-11
L a-57
L b31
2-12
L a-72
L b31
2-13
L a-119
L b31
2-14
L a-128
L b31
2-15
L a-129
L b31
2-16
L a-130
L b31
2-17
L a-133
L b31
2-18
L a-136
L b31
2-19
L a-137
L b31
2-20
L a-141
L b31
2-21
L a-146
L b31
2-22
L a-181
L b31
2-23
L a-194
L b31
2-24
L a-195
L b31
2-25
L a-204
L b31
2-26
L a-205
L b31
2-41
L a-36
L b57
2-42
L a-37
L b57
2-43
L a-41
L b57
2-44
L a-43
L b57
2-45
L a-45
L b57
2-46
L a-53
L b57
2-47
L a-57
L b57
2-47
L a-72
L b57
2-49
L a-119
L b57
2-50
L a-128
L b57
2-51
L a-129
L b57
2-52
L a-130
L b57
2-53
L a-133
L b57
2-54
L a-136
L b57
2-55
L a-137
L b57
2-56
L a-141
L b57
2-57
L a-146
L b57
2-58
L a-181
L b57
2-59
L a-194
L b57
2-60
L a-195
L b57
2-61
L a-204
L b57
2-62
L a-205
L b57
2-77
L a-36
L b88
2-78
L a-37
L b88
2-79
L a-41
L b88
2-80
L a-43
L b88
2-81
L a-45
L b88
2-82
L a-53
L b88
2-83
L a-57
L b88
2-84
L a-72
L b88
2-85
L a-119
L b88
2-86
L a-128
L b88
2-87
L a-129
L b88
2-88
L a-130
L b88
2-89
L a-133
L b88
2-90
L a-136
L b88
2-91
L a-137
L b88
2-92
L a-141
L b88
2-93
L a-146
L b88
2-94
L a-181
L b88
2-95
L a-194
L b88
2-96
L a-195
L b88
2-97
L a-204
L b88
2-98
L a-205
L b88
2-113
L a-36
Lb 122
2-114
L a-37
L b122
2-115
L a-41
Lb 122
2-116
L a-43
L b122
2-117
L a-45
Lb 122
2-118
L a-53
L b122
2-119
L a-57
Lb 122
2-120
L a-72
L b122
2-121
L a-119
Lb 122
2-122
L a-128
L b122
2-123
L a-129
Lb 122
2-124
L a-130
L b122
2-125
L a-133
Lb 122
2-126
L a-136
L b122
2-127
L a-137
Lb 122
2-128
L a-141
L b122
2-129
L a-146
Lb 122
2-130
L a-181
L b122
2-131
L a-194
Lb 122
2-132
L a-195
L b122
2-133
L a-204
Lb 122
2-134
L a-205
L b122
2-149
L a-36
L b126
2-150
L a-37
L b126
2-151
L a-41
L b126
2-152
L a-43
L b126
2-153
L a-45
L b126
2-154
L a-53
L b126
2-155
L a-57
L b126
2-156
L a-72
L b126
2-157
L a-119
L b126
2-158
L a-128
L b126
2-159
L a-129
L b126
2-160
L a-130
L b126
2-161
L a-133
L b126
2-162
L a-136
L b126
2-163
L a-137
Lb 126
2-164
L a-141
L b126
2-165
L a-146
L b126
2-166
L a-181
L b126
2-167
L a-194
L b126
2-168
L a-195
L b126
2-169
L a-204
L b126
2-170
L a-205
L b126
2-185
L a-36
L b212
2-186
L a-37
L b212
2-187
L a-41
L b212
2-188
L a-43
L b212
2-189
L a-45
L b212
2-190
L a-53
L b212
2-191
L a-57
L b212
2-192
L a-72
L b212
2-193
L a-119
L b212
2-194
L a-128
L b212
2-195
L a-129
L b212
2-196
L a-130
L b212
2-197
L a-133
L b212
2-198
L a-136
L b212
2-199
L a-137
L b212
2-200
L a-141
L b212
2-201
L a-146
L b212
2-202
L a-181
L b212
2-203
L a-194
L b212
2-204
L a-195
L b212
2-205
L a-204
L b212
2-206
L a-205
L b212
wherein the Compound 2-217 to Compound 2-223, Compound 2-229 to Compound 2-237, Compound 2-243 to Compound 2-251, Compound 2-257 to Compound 2-265, Compound 2-271 to Compound 2-279, Compound 2-285 to Compound 2-293 and Compound 2-299 to Compound 2-300 have the structure of Ir(L a ) 2 (L b ), wherein the two L a are different, and the L a and L b respectively correspond to structures listed in the following table:
Compound
Compound
No.
L a
L a
L b
No.
L a
L a
L b
2-217
L a-133
L a-41
L b31
2-218
L a-133
L a-43
L b31
2-219
L a-133
L a-136
L b31
2-220
L a-133
L a-137
L b31
2-221
L a-133
L a-146
L b31
2-222
L a-133
L a-204
L b31
2-223
L a-133
L a-205
L b31
2-229
L a-41
L a-136
L b31
2-230
L a-41
L a-137
L b31
2-231
L a-133
L a-41
L b57
2-232
L a-133
L a-43
L b57
2-233
L a-133
L a-136
L b57
2-234
L a-133
L a-137
L b57
2-235
L a-133
L a-146
L b57
2-236
L a-133
L a-204
L b57
2-237
L a-133
L a-205
L b57
2-243
L a-41
L a-136
L b57
2-244
L a-41
L a-137
L b57
2-245
L a-133
L a-41
L b88
2-246
L a-133
L a-43
L b88
2-247
L a-133
L a-136
L b88
2-248
L a-133
L a-137
L b88
2-249
L a-133
L a-146
L b88
2-250
L a-133
L a-204
L b88
2-251
L a-133
L a-205
L b88
2-257
L a-41
L a-136
L b88
2-258
L a-41
L a-137
L b88
2-259
L a-133
L a-41
L b122
2-260
L a-133
L a-43
L b122
2-261
L a-133
L a-136
L b122
2-262
L a-133
L a-137
L b122
2-263
L a-133
L a-146
L b122
2-264
L a-133
L a-204
L b122
2-265
L a-133
L a-205
L b122
2-271
L a-41
L a-136
L b122
2-272
L a-41
L a-137
L b122
2-273
L a-133
L a-41
L b126
2-274
L a-133
L a-43
L b126
2-275
L a-133
L a-136
L b126
2-276
L a-133
L a-137
L b126
2-277
L a-133
L a-146
L b126
2-278
L a-133
L a-204
L b126
2-279
L a-133
L a-205
L b126
2-285
L a-41
L a-136
L b126
2-286
L a-41
L a-137
L b126
2-287
L a-133
L a-41
L b212
2-288
L a-133
L a-43
L b212
2-289
L a-133
L a-136
L b212
2-290
L a-133
L a-137
L b212
2-291
L a-133
L a-146
L b212
2-292
L a-133
L a-204
L b212
2-293
L a-133
L a-205
L b212
2-299
L a-41
L a-136
L b212
2-300
L a-41
L a-137
L b212 .
25 . The electroluminescent device of claim 23 , wherein the second compound has the structure of Ir(L a ) 2 (L b ), wherein L a is, at each occurrence identically or differently, selected from any one or any two of the group consisting of L a-35 to L a-223 and L b is selected from any one of the group consisting of L b1 to L b322 .
26 . The electroluminescent device of claim 1 , wherein the organic layer is a light-emitting layer, the first compound is a host material, and the second compound is a light-emitting material.
27 . The electroluminescent device of claim 26 , wherein the device emits red light or white light.
28 . A display assembly, comprising the electroluminescent device of claim 1 .
29 . The electroluminescent device of claim 1 , wherein R and R f are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, a cyano group, a hydroxyl group, a sulfanyl group and combinations thereof.
30 . A compound combination, comprising a first compound and a second compound, wherein
the first compound has a structure of H-L-E; H has a structure represented by Formula 1-a:
in Formula 1-a, A 1 , A 2 and A 3 are, at each occurrence identically or differently, selected from CR, and F 1 to F 10 are, at each occurrence identically or differently, selected from CR f ;
E has a structure represented by Formula 2-d:
in Formula 2-d, Z 2 and Z 4 are each independently selected from CR z ;
L is selected from substituted or unsubstituted arylene having 6 to 30 carbon atoms, substituted or unsubstituted heteroarylene having 3 to 30 carbon atoms or a combination thereof;
R, R f and R z are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, a cyano group, a hydroxyl group, a sulfanyl group, and combinations thereof; and
adjacent substituents R, R f can be optionally joined to form a ring;
the second compound is a metal complex having a general formula of Ir(L a ) 2 (L b );
wherein L a and L b are a first ligand and a second ligand coordinated to the Ir, respectively;
L a and L b can be optionally joined to form a multidentate ligand;
the multiple L a may be the same or different;
the L a has a structure represented by Formula 3-1 or Formula 3-3:
wherein,
the ring E is selected from a benzene ring;
R e represents, at each occurrence identically or differently, mono-substitution, multiple substitutions or non-substitution;
X 11 to X 14 are, at each occurrence identically or differently, selected from CR x1 ; X 31 to X 34 are, at each occurrence identically or differently, selected from CR x3 ;
Y 3 and Y 4 are, at each occurrence identically or differently, selected from CR d ;
R x1 , R x3 , R d and R e are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, and combinations thereof;
adjacent substituents R x1 , R d and R e can be optionally joined to form a ring;
when R x3 is selected from substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, or substituted or unsubstituted amino having 0 to 20 carbon atoms, adjacent substituents R x3 can be optionally joined to form a ring;
L b has the following structure:
R a , R b and R c represent, at each occurrence identically or differently, mono-substitution, multiple substitutions or non-substitution;
X c and X d are O;
R a , R b and R c , are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, a cyano group, and combinations thereof;
in structures of L b , adjacent substituents R a , R b , R c , can be optionally joined to form a ring;
and, the following case is not comprised: the first compound is
while the second compound isCited by (0)
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